The Portland Trail Blazers made headlines this offseason by trading Anfernee Simons to the Boston Celtics in exchange for Jrue Holiday. While the initial deal included two second-round picks heading to Boston, it was later revised into a straight swap due to concerns over Holiday’s medical history.
Boston’s decision to move Holiday wasn’t a shock, especially after Jayson Tatum’s Achilles injury derailed the team’s title hopes. What caught many off guard was Portland reacquiring the 35-year-old guard despite being in the midst of a rebuild. For the Blazers, Holiday’s value lies more in his leadership for a young roster than in contending for a championship.
Even so, the trade doesn’t look bad for Portland when compared to Boston’s current struggles with Simons. The Celtics have reportedly been shopping the guard but have found no takers for the $27.7 million he’s owed in the final year of his deal.
Simons’ scoring consistency has raised questions, as he dipped to 19.3 points per game last season after back-to-back years above 21. Though still talented, committing long-term money to him could be risky for Boston, making him a potential trade candidate again before the February deadline.
If Simons doesn’t impress early, the Celtics may regret the move, particularly given the cost and uncertainty around his future. Meanwhile, Portland’s timing in dealing him could ultimately look savvy.
Critics might question why the Blazers brought back Holiday, but at least they avoided being stuck with a hefty contract. If Simons falters in Boston, the trade could end up looking like a win for Portland.
